N¹-(7-chloroquinolin-4-yl)heptane-1,7-diamine | 102882-13-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N¹-(7-chloroquinolin-4-yl)heptane-1,7-diamine
• 英文别名: N'-(7-chloroquinolin-4-yl)heptane-1,7-diamine
• CAS: 102882-13-3
• 化学式: C₁₆H₂₂ClN₃
• 分子量: 291.824
• InChiKey: BRLZBAKTJKUPIL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  50.9
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N¹-(7-chloroquinolin-4-yl)heptane-1,7-diamine 在 sodium periodate 、 碳酸氢钠 作用下， 以 四氢呋喃 、 phosphate buffer 为溶剂， 生成 N-[7-(7-Chloro-quinolin-4-ylamino)-heptyl]-2-oxo-acetamide
  参考文献：
  名称：

  Design, synthesis and antimalarial activity of a glyoxylylhydrazone library

  摘要：

  Synthesis of a new family of quinolylhydrazone derivatives and evaluation of their activity against a chloroquine-resistant strain of Plasmodium falciparum are described. The best compound displayed an activity 6-fold higher than chloroquine. None of the active compounds were found to inhibit beta-hematin formation in vitro in the same range as chloroquine and five among them displayed lower calculated vacuolar accumulation ratios, suggesting the implication of a different mechanism of action. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.06.056
• 作为产物：
  描述：

  4,7-二氯喹啉 、 1,7-二氨基庚烷 以 neat (no solvent) 为溶剂， 以85 %的产率得到N¹-(7-chloroquinolin-4-yl)heptane-1,7-diamine
  参考文献：
  名称：

  发现由三唑并嘧啶和吡唑并嘧啶支架连接的新型哌喹杂交类似物，具有抗疟原虫和传递阻断活性

  摘要：

  世界卫生组织 （WHO） 估计，2021 年全球有 2.47 亿例疟疾病例，与 2020 年相比增加了 200 万例。具体标准强调了开发新型抗疟药的迫切需要，包括需要避免交叉耐药性的新作用方式、提供单剂量治疗的能力以及对异性血和性血阶段的疗效。受我们研究小组使用 [1,2,4] 三唑并[1,5-a] 嘧啶和吡唑并[1,5-a] 嘧啶衍生物获得的可喜结果的激励，我们选择了这些分子支架作为设计两个新系列哌喹类似物的基础作为潜在的抗疟候选药物。最初的杂交系列是通过用 1,2,4-三唑并[1,5-a]嘧啶或吡唑并[1,5-a]嘧啶核取代哌喹的一个喹啉环来设计的。为了连接杂环系统，在喹啉的 4 位置引入具有 3、4 或 7 个亚甲基碳的垫片。在第二个系列中，我们使用哌嗪作为间隔物，将 1,2,4-三唑并[1,5-a] 嘧啶或吡唑并[1,5-a] 嘧啶基团连接到喹啉核心，通过刚性间隔物有效地合并两个药

  DOI：

  10.1016/j.ejmech.2024.116163

文献信息

• 一种喹啉-1，2，4-三嗪杂合体、制备方法及其应用
  申请人：江苏海洋大学

  公开号：CN114133377B

  公开（公告）日：2023-05-02

  本发明涉及药物化学技术领域，特别涉及一种喹啉‑1，2，4‑三嗪杂合体、制备方法及其应用。所述氯‑喹啉与1，2，4‑三嗪杂合体结构如式I所示。且本发明喹啉‑1，2，4‑三嗪杂合体的制备方法为：式II所示的化合物与式III所示的化合物在碳酸钠或碳酸铯的存在下反应得到。本发明的喹啉‑1，2，4‑三嗪杂合体具有很好的抗疟活性。
• Quinoline–Pyrimidine Hybrids: Synthesis, Antiplasmodial Activity, SAR, and Mode of Action Studies
  作者：Kamaljit Singh、Hardeep Kaur、Peter Smith、Carmen de Kock、Kelly Chibale、Jan Balzarini

  DOI：10.1021/jm4014778

  日期：2014.1.23

  For the treatment of malaria which affects nearly 200 million people each year and the continued exacerbation by the emergence of drug resistance to most of the available antimalarials, the "covalent bitherapy" suggests hybrid molecules to be the next-generation antimalarial drugs. In this investigation, new hybrids of 4-aminoquinoline and pyrimidine moieties that show antiplasmodial activity in the nM range against chloroquine-resistant as well as chloroquine-sensitive strains of Plasmodium falciparum have been prepared. Cytotoxicity evaluation and mode of action of most potent hybrid molecule have been conducted.
• Nitrogen Mustard Analogs of Antimalarial Drugs¹
  作者：Richard M. Peck、Robert K. Preston、Hugh J. Creech

  DOI：10.1021/ja01524a041

  日期：1959.8
• [EN] NUCLEOSIDE AND NUCLEOTIDE CONJUGATE COMPOUNDS AND USES THEREOF<br/>[FR] COMPOSÉS CONJUGUÉS DE NUCLÉOSIDE ET DE NUCLÉOTIDE ET LEURS UTILISATIONS
  申请人：REYOUNG CORP

  公开号：WO2021202669A3

  公开（公告）日：2021-12-02
• Similar Structure−Activity Relationships of Quinoline Derivatives for Antiprion and Antimalarial Effects
  作者：Ralf Klingenstein、Patricia Melnyk、S. Rutger Leliveld、Adina Ryckebusch、Carsten Korth

  DOI：10.1021/jm0602763

  日期：2006.8.1

  Prion diseases are invariably fatal neurodegenerative diseases, in which the infectious agent consists of PrPSc, a pathogenic misfolded isoform of the normal cellular prion protein ( PrPC). Until now, no pharmacological options exist for these novel pathogens. Here we describe the screening of a series of polyquinolines and quinolines linked to a large variety of terminal groups for their ability to cure a persistently prion infected cell line (ScN2a). Several compounds showed antiprion activity in the nanomolar range. The most active molecule, named 42, had a half-effective concentration (EC50) for antiprion activity of 50 nM. In a library of quinoline derivatives we were able to identify several structure-activity relationships (SAR). Remarkably, antiprion SAR in ScN2a cells were similar to antimalarial SAR in a cell model of malaria, particularly for the sulfonamide quinoline derivatives, suggesting that some molecular targets of antiprion and antimalarial substances overlap.